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Information × Registration Number 0220U103063, 0115U004731 , R & D reports Title Synthesis of heterocyclic compounds on the basis of N-substituted 1,4-quinoneimines. popup.stage_title Head Avdeenko Anatoly P., Кандидат хімічних наук Registration Date 24-07-2020 Organization Donbass State Engineering Academy popup.description2 Object of research: unsubstituted and halogensubstituted in the quinoid ring N-acyl-1,4-benzo-quinoneimines. Objective: to find the rules of the influence of the steric and donor-acceptor properties of the substituents near the nitrogen atom in N-acyl-1,4-benzoquinonemjnoimines on their reactivity to nucleophiles, and also the synthesis of new heterocyclic potentially bioactive compounds on their basis. Research methods: organic synthesis, physical and chemical methods for the investigation of organic compounds: IR, NMR 1H, NMR 13C spectroscopy, elemental analysis, X-ray diffraction analysis, thin layer and column chromatography. Results: new heterocyclic compounds on the basis of N-acyl-1,4-benzoquinoniminoimines were synthesized. Their structures were proved by the spectral (IR, PMR, NMR 13C) data and elemental analysis. In the interaction of N -acyl-1,4-benzoquinone monoimin with potassium rhodanite, depending on the energy of the LUMO of the original quinone monoimin, benzo [d] [1,3] oxathiol-2-ones and benzo [d] oxazol-2 (3H) - derivatives were obtained thiones. At the first stage of the reaction, the high value of the energy of the LUMO promotes the addition of rodanide ion to the nitrogen atom, the low value to the addition by the sulfur atom.. As a result of the action of bromine on the halogen-containing N-acetyl -1,4-benzoquinoniminoimines having one free position of 3 or 5 of the quinidic nucleus, 6-hydroxy-2-methyl(aryl)-1,3-benzoxazoles are obtained, which is quite a simple method of synthesis of the latter. As a result of the reaction of N-acyl-1,4-benzoquinonemonimines with enamines, in particular 4-(p-toluidino pent-3-en-2-one and ethyl 3-(phenylamino)bute-2-enoate, by the mechanism of the reaction of Nenitsesku, derivatives of benzofuran were obtained. Efficiency: heterocyclic compounds based on N-acyl-1,4-benzoquinonmonoimines are potential biologically active compounds and can be used as drugs, pesticides. Product Description popup.authors popup.nrat_date 2020-10-01 Close